Benzathine → Ethyl 1,4-dibenzyl-3-oxopiperazine-2-carboxylate

HRID 1035286

Reaktionsgleichung

Reaktionsgleichung von HRID 1035286
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:20]([C:26]([O:28]CC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(#N)C.[OH-].[Na+]>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:26](=[O:28])[CH:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 8793BenzathineHCID 69637Diethyl bromomalonate

Produkt 1

HCID 15645950Ethyl 1,4-dibenzyl-3-oxopiperazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of N,N′-dibenzylethylenediamine (14.12 mL, 60.2 mmol) in acetonitrile (100 mL) was added diethyl bromomalonate (5.14 mL, 30.1 mmol), and the mixture was heated with an oil bath at 90° C. (reflux) for 7 hours. The solvent was evaporated to provide a residue that was dissolved in 1 M NaOH (aqueous), and the mixture was extracted with ethyl acetate twice, dried over Na2SO4, and the solvent was evaporated. The crude mixture was purified by silica gel chromatography (Analogix IntelliFlash 280, SF40-150) eluting with 15%-30% ethyl acetate/hexanes to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.38-7.20 (m, 10H), 4.54 (dd, J=15.0, 154.2, 2H), 4.20-4.10 (m, 2H), 4.03 (q, J=7.1, 1H), 3.96 (s, 1H), 3.61 (dd, J=13.5, 41.7, 2H), 3.27-3.14 (m, 2H), 3.05-2.95 (m, 1H), 2.60-2.52 (m, 1H), 1.23 (t, J=7.1, 3H); MS (ESI+) m/z 353.0 (M+H)+.

Aufarbeitung

  1. temperature(reflux) for 7 hours
  2. customThe solvent was evaporated
  3. customto provide a residue that
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated
  7. customThe crude mixture was purified by silica gel chromatography (Analogix IntelliFlash 280, SF40-150)
  8. washeluting with 15%-30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f8dff528f719486c8df628f1de96d9a3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546377B2

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